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A small amount of backstory (I love typing so much). We have an old red dragon living in the basement of our castle. He came to us as a human and a priest, but we forced his hand into revealing himself. He says he intends us no harm, but I'm not as trustworthy as some of my team. At this point, he is not actively attacking us, and we know a bit of his motivations, but I strongly feel that he is going to betray us.
So, is it possible to outsmart him? Have a contingency, somehow? He's old, and of course has a ridiculous cr (for our level, which is 5), so waiting will obviously be a part of the plan. He still doesn't detect as evil in his dragon or human form, but I definitely don't trust him. Can we even reform him? Are there ANY possibilities of getting an advantage over him at this level?
At level 5 I'd say your only hope is to outsmart him.
The quick answer is "probably not."
You could try to nail him with charm or enchantment spells and hope the GM rolls a 1. That's a pretty good way to tick him off though.
If you really feel it is necessary to do something about the dragon, I'd recommend finding a high level NPC or NPCs and convincing them that the dragon is a danger.
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I figured as much. My party members aren't convinced, and are sure that he's either not evil, or can be easily changed (citing that there are certainly red dragons that aren't evil, like silver dragons can be not good). I just am hoping for some kind of contingency, because I don't think my GM is mean enough to have him turn on us this early unless we do something stupid.
If you have to ask... :-)
Expeditious retreat is a good contingency.
I'd recommend scanning him with some other divinations besides detect evil. As an Old Dragon, however, the CR is a lot higher than 5, so crossing him is a Very Bad Idea. Yes it is well within the dragon's capabilities to thwart your puny low level divination spells - retry them each time you advance in level and salt away anti red dragon gear for the day when you feel that you must smite the dragon mightily.
If you must throw down with the Old Red Dragon, your only hope is thorough preparation: resist energy, protection from energy, stoneskin, heroism, false life, prayer ... you'll desperately need a permanently magical weapon and preferably several. You will also want to slather on anything that penalizes the dragon's Dexterity as fast as possible - tanglefoot bags, nets of sufficient size (once you get telekinesis), clumsiness magic, flasks of liquid ice, good old fashioned acid, etc.
You'll also need to invest in top shelf locks on your chests that store all your dragonslaying goodies. I recommend six to ten locks per chest, all of the DC 40 variety. Line the chest with a thin sheet of lead on all facings. If possible, maintain ongoing alarm spells and ward with the noisiest magic you have, although explosive runes has the advantage of being very cheap (read: free). Nesting a series of smaller, tougher chests inside larger, flimsier chests - the key component of which is the obscene number of DC 40 locks in combination with lead lining and assorted protective spells - is an excellent method of protecting stuff you don't need to get to in a particular hurry.
Having said all of that, it is very possible to reform the dragon, especially since the monster hasn't already incinerated the lot of you in your sleep and taken your stuff. Engage in dialog regularly (and as the player, take notes, compare them as time progresses) with the dragon. Test him from time to time with an expendable fair maiden or low-ranking princess. Set a big bag of shiny gold bling where it can see it - you want to be a fair distance away with a spyglass so that it's blindsense doesn't tell it that you're close enough to watch. I recommend a murder hole with a view, a spyglass and both no scent and silence spells. If some one else snatches the bag o' swag, your minions can reacquire and replace the bag at a later time.
Pay careful attention to thieving, disappearing livestock and so on.
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The good part is that his motivations as we know them are going to keep him from attacking us for a while. The bad part means that we might be hosed if we can't handle ourselves. His dad (a red wyrm, most likely) is looking to kill him when he wakes up from his sleep, and the old dragon wants to build an army with us to kill him. The Wyrm will most likely attack us anyway, as our land used to be under his domain when he first went to sleep, so he will likely be wanting it back.
And those are some fantastic ideas, Turin, thanks a ton!